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Chapter 5: Q.36 (page 205)

a) Locate the stereogenic centers in the ball-and-stick model of ezetimibe (trade name Zetia), a cholesterol-lowering drug. (b) Label each stereogenic center as R or S.

Short Answer

Expert verified

A stereogenic center is a point in a molecule in which one carbon atom is bonded to four different groups of atoms. This carbon atom is considered to be asymmetrical in nature.

By interchanging any group on the asymmetrical carbon, it leads to the formation of a stereoisomer.

Step by step solution

01

Meaning of stereogenic centers

A stereogenic center is a point in a molecule in which one carbon atom is bonded to four different groups of atoms. This carbon atom is considered to be asymmetrical in nature.

By interchanging any group on the asymmetrical carbon, it leads to the formation of a stereoisomer.

02

Stereogenic centers in ezetimibe

The structure of the ezetimibe molecule is shown below:

It has three stereocenters, as shown in the above structure.

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Most popular questions from this chapter

A limited number of chiral compounds having no stereogenic centers exist. For example, although A is achiral, constitutional isomer B is chiral. Make models and explain this observation. Compounds containing two double bonds that share a single carbon atom are called allenes. Locate the allene in the antibiotic mycomycin and decide whether mycomycin is chiral or achiral.

HC≡C-C≡C-CH=C=CH-CH=CH-CH=CH-CH2CO2H

Which group in each pair is assigned the higher priority?

a. -CH3,-CH2CH3

b. -I,-Br

c. -H,-D

d. -CH2Br,-CH2CH2Br

e. localid="1648296449951" -CH2Cl,-CH2CH(CH3)2

f.-CH2OH,-CHO

Rank the following groups in order of decreasing priority.

  1. -F,-NH2,-CH3,-OH
  2. -CH3,-CH2CH3,-CH2CH2CH3,-(CH2)3CH3
  3. -NH2,-CH2NH2,-CH3,-CH2NHCH3
  4. -COOH,-CH2OH,-H,-CHO
  5. -Cl,-CH3,-SH,-OH
  6. -C≡CH,-CH(CH3)2,-CH2CH3,-CH=CH2

Cellulose is water insoluble, despite its many OH groups. Considering its three-dimensional structure, why do you think this is so?

Saquinavir (trade name Invirase) is a protease inhibitor, used to treat HIV (human immunodeficiency virus).

  1. Locate all stereogenic centers in saquinavir, and label each stereogenic center as R and S.
  2. Draw the enantiomer of saquinavir.
  3. Draw a diastereomer of saquinavir.
  4. Draw a constitutional isomer that contains at least one different functional group.
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